| 1 | Fri 13 Jul 2018 | 4-0 v Cirencester TownCirencester Town 0-4 Cheltenham Town | Friendly |
| 2 | Sat 21 Jul 2018 | 0-3 v Birmingham CityCheltenham Town 0-3 Birmingham City | Friendly |
| 3 | Tue 21 Aug 2018 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Cheltenham Town | Sky Bet League Two |
| 4 | Sat 3 Nov 2018 | 2-2 v Mansfield TownCheltenham Town 2-2 Mansfield Town | Sky Bet League Two |
| 5 | Tue 13 Nov 2018 | 2-0 v Coventry CityCheltenham Town 2-0 Coventry City | Checkatrade Trophy Southern Group E |
| 6 | Tue 4 Dec 2018 | 1-1 v Newport CountyCheltenham Town 1-1 Newport County | Checkatrade Trophy Second Round |
| 7 | Sat 15 Dec 2018 | 2-2 v Port ValePort Vale 2-2 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 29 Dec 2018 | 2-2 v Forest Green RoversCheltenham Town 2-2 Forest Green Rovers | Sky Bet League Two |
| 9 | Tue 1 Jan 2019 | 4-1 v Yeovil TownYeovil Town 1-4 Cheltenham Town | Sky Bet League Two |
| 10 | Tue 19 Feb 2019 | 2-0 v Cambridge UnitedCheltenham Town 2-0 Cambridge United | Sky Bet League Two |
| 11 | Sat 13 Apr 2019 | 1-1 v Lincoln CityLincoln City 1-1 Cheltenham Town | Sky Bet League Two |
| 12 | Mon 22 Apr 2019 | 0-4 v MorecambeMorecambe 4-0 Cheltenham Town | Sky Bet League Two |
| 13 | Sat 27 Apr 2019 | 3-2 v Swindon TownCheltenham Town 3-2 Swindon Town | Sky Bet League Two |
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